Fluorene-containing polymers and compounds useful in the preparation thereof

Abstract

A compound of the formula:and compounds of the formulas:whereinR1 is independently in each occurrence C1-20 hydrocarbyl or C1-20 hydrocarbyl containing one or more S, N, O, P or Si atoms, C4-16 hydrocarbyl carbonyloxy, C4-16 aryl(trialkylsiloxy) or both R1 may form with the 9-carbon on the fluorene ring a C5-20 ring structure or a C4-20 ring structure containing one or more heteroatoms of S, N or O;R2 is independently in each occurrence C1-20 hydrocarbyl, C1-20 hydrocarbyloxy, C1-20 thioether, C1-20 hydrocarbylcarbonyloxy or cyano;R3 is independently in each occurrence C1-20 hydrocarbyl or C1-20 hydrocarbyl substituted with di(C1-20 alkyl)amino, C1-20 hydrocarbyloxy or C1-20 hydrocarbyl or tri(C1-10 alkyl)siloxy;a is independently in each occurrence 0 or 1;X is independently in each occurrence a halogen moiety; andZ is independently in each occurrence -B(OH)2, -B(OR4)2 or whereinR4 is independently in each occurrence a C1-10 alkyl group andR5 is independently in each occurrence a C2-10 alkylene group.

What is claimed is:  
     
       1. A composition containing polymers which have at least ten groups of the formula:                    
       and a polydispersity of less than 5, wherein R 1  is independently in each occurrence C 1-20  hydrocarbyl or C 1-20  hydrocarbyl containing one or more S, N, O, P or Si atoms, C 4-16  hydrocarbyl carbonyloxy, C 4-16  aryl(trialkylsiloxy) or both R 1  may form with the 9-carbon on the fluorene ring a C 5-20  ring structure or a C 4-20  ring structure containing one or more heteroatoms of S, N or O;  
       R 2  is independently in each occurrence C 1-20  hydrocarbyl, C 1-20  hydrocarbyloxy, C 1-20  thioether, C 1-20  hydrocarbylcarbonyloxy or cyano; and  
       a is independently in each occurrence, 0 or 1, wherein substantially all the polyfluorene groups (IV) are connected through the 2 and 7 carbon atoms and wherein, in addition to the groups of formula IV, the polymer includes at least one other conjugated monomer group.  
     
     
       2. The composition of  claim 1  which contains polymers having at least 30 groups of Formula (IV). 
     
     
       3. The composition of  claim 1  wherein R 1  is C 1-12  alkyl. 
     
     
       4. The composition of  claim 3  wherein R 1  is C 6-12  alkyl and a is 0. 
     
     
       5. The composition of  claim 4  which contains polymers having at least 30 groups of Formula (IV). 
     
     
       6. A film prepared from the composition of  claim 1 . 
     
     
       7. The composition of  claim 1  wherein the other conjugated monomer group is selected from stilbene, tolan, C 6-20  mononuclear or polynuclear aromatic hydrocarbons, C 2-10  mononuclear or polynuclear heterocycles, and tertiary aromatic amines. 
     
     
       8. The composition of  claim 1  wherein the other conjugated monomer group is selected from benzene; naphthalene; acenaphthene; phenanthrene; anthracene; fluoranthene; pyrene; rubrene; chrysene; furan; thiophene; pyrrole; oxazol;, isooxazole; thiazole; isothiazole; imidazole; oxadiazoles; thiadiazole, pyrazoles; pyridine; pyridazine; pyrimidine; pyrazine; triazines; tetrazines; benzoxazole; benzothiazole; benzimidazole; quinoline; isoquinoline; cinnoline; quinazoline; quioxaline; phthalazine; benzothiadiazole; benzotriazines; phenazine; phenanthridine; acridine; carbozole; diphenyleneoxide; triphenyl amine; alkyldiaryl amines; N,N,N′,N′-tetraphenylbenzidine; and N,N,N′,N′-tetraphenyl-1,4-phenylediamine. 
     
     
       9. The composition of  claim 1  wherein the polymer has a weight average molecular weight of at least 20,000 Daltons and a polydispersity less than 3.0. 
     
     
       10. The composition of  claim 9  wherein the polymer has a polydispersity less than 2.5. 
     
     
       11. The composition of  claim 3  wherein the other conjugated monomer group is selected from stilbene, tolan, C 6-20  mononuclear or polynuclear aromatic hydrocarbons, C 2-10  mononuclear or polynuclear heterocycles, and tertiary aromatic amines. 
     
     
       12. The composition of  claim 3  wherein the other conjugated monomer group is selected from benzene; naphthalene; acenaphthene; phenanthrene; anthracene; fluoranthene; pyrene; rubrene; chrysene; furan; thiophene; pyrrole; oxazol;, isooxazole; thiazole; isothiazole; imidazole; oxadiazoles; thiadiazole, pyrazoles; pyridine; pyridazine; pyrimidine; pyrazine; triazines; tetrazines; benzoxazole; benzothiazole; benzimidazole; quinoline; isoquinoline; cinnoline; quinazoline; quioxaline; phthalazine; benzothiadiazole; benzotriazines; phenazine; phenanthridine; acridine; carbozole; diphenyleneoxide; triphenyl amine; alkyldiaryl amines; N,N,N′,N′-tetraphenylbenzidine; and N,N,N′,N′-tetraphenyl-1,4-phenylediamine.